Trifluoroacetic acid → HCID 57991938, compound

HRID 2075336Notes

Reaction equation

HRID 2075336 reaction equation
[Cl:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]2[S:8][C:9]([C:11]3[S:15][C:14]([NH:16][CH2:17][C@@H:18]([NH:30]C(=O)OC(C)(C)C)[CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=4)=[N:13][N:12]=3)=[CH:10][C:3]=12.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:30][C@@H:18]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:27])([F:29])[F:28])[CH:21]=1)[CH2:17][NH:16][C:14]1[S:15][C:11]([C:9]2[S:8][C:4]3=[CH:5][N:6]=[CH:7][C:2]([Cl:1])=[C:3]3[CH:10]=2)=[N:12][N:13]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86636673HCID 86636673, compound

Product 1

HCID 57991938HCID 57991938, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl (S)-1-(5-(4-chlorothieno[2,3-c]pyridin-2-yl)-1,3,4-thiadiazol-2-ylamino)-3-(3-(trifluoromethyl)phenyl)propan-2-ylcarbamate (0.070 g, 0.12 mmol) was treated with 1 mL TFA in 1 mL DCM for 30 minutes. After removing the solvent, the residue was mixed with 10 mL 2M ammonia in MeOH. The solvent was removed again and the remaining residue was subjected to a silica gel flash chromatography separation using 3.5% 2M ammonia MeOH solution in DCM as the eluant. An-off white solid was obtained as the pure product (0.03 g, y=52%). LCMS (API-ES) m/z (%): 470.1 (100%, M++H); 1H NMR (300 MHz, CDCL3) δ ppm 1.48-1.82 (b, 3H) 2.72 (dd, J=13.56, 8.48 Hz, 1H) 3.00 (dd, J=13.66, 4.99 Hz, 1H) 3.26-3.35 (m, 1H) 3.40-3.50 (m, 1H) 3.61 (dd, J=12.72, 3.67 Hz, 1H) 7.41-7.56 (m, 6H) 8.46 (s, 1H) 8.95 (s, 1H).

Workup

  1. customAfter removing the solvent
  2. additionthe residue was mixed with 10 mL 2M ammonia in MeOH
  3. customThe solvent was removed again
  4. customthe remaining residue was subjected to a silica gel flash chromatography separation
  5. customAn-off white solid was obtained as the pure product (0.03 g, y=52%)

Sources & evidence

ORD record
ord-b710a2858cf74f9aa1f9f996ba0051d6
Source dataset
uspto-grants-2011_04
Patent number
US07919504B2

Reaction notes

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